Conventionally, the following method for producing an optically active β-amino alcohol has been known in the art:    1) producing an α-oxime ketone from ketone and alkyl nitrite; producing a β-oxime alcohol by asymmetric hydrogenation in the presence of a transition metal catalyst; and reducing the oxime group to produce a β-amino alcohol (Japanese Unexamined Patent Application Publication No. 5-4948).
However, this method uses explosive alkyl nitrite, which is difficult to handle, to produce explosive α-oxime ketones and is thus not suitable for industrial applications.
As the method for producing an optically active 1-aryl-2-amino-1-ethanol derivative, the following is known in the art:    2) producing a ketone derivative by reacting benzene with an acid chloride of L-alanine and reducing the carbonyl group to produce (1R,2S)-1-phenyl-2-amino-1-propanol((−)-norephedrine) (Japanese Unexamined Patent Application Publication No. 62-209047);    3) producing N,N-dibenzylalaninal from L-alanine, reacting the N,N-dibenzylalaninal with a phenyl magnesium reagent, and performing debenzylation to obtain (1R,2S)-1-phenyl-2-amino-1-propanol((−)-norephedrine) (European Patent No. 288764, U.S. Pat. No. 4,990,669).
However, these methods are limited to the production of the (1R,2S)-1-phenyl-2-amino-1-propanol((−)-norephedrine) and cannot easily be applied to synthesis of optically active 1-aryl-2-amino-1-ethanol derivatives having substituents in the benzene rings.
As the method for producing an optically active 1-(4-hydroxyphenyl)-2-amino-1-ethanol derivative, the following method has been known:    4) producing a salt from tartaric acid and racemic erythro-1-(4-hydroxyphenyl)-2-amino-1-propanol (p-hydroxynorephedrine), followed by separation (J. Med. Chem., 1977, 20, 978).
However, in this method, the racemic mixture to be separated is synthesized through multiple stages, and this method is thus not industrially advantageous. Moreover, expensive D-tartaric acid is necessary in order to obtain (1R,2S)-1-(4-hydroxyphenyl)-2-amino-1-propanol.